Steakhouses in Jackson Park

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Jackson Grill: A User's Guide

Acclaimed Supper Club | Steaks and Seafood | Massive Portions | Brandy Old-Fashioned Cocktails | Retro Vibe

Sample Menu

  • Appetizer: hand-cut duck-fat fries served with housemade aioli
  • Entree: 24-ounce Black Angus bone-in rib eye with gorgonzola butter
  • Side: garlic mashed potatoes
  • Cocktail: brandy old-fashioned sour

    The Vibe: If one phrase best sums up Jackson Grill, it's "old fashioned." This descriptor applies equally to the decor of candlelit white linens and to the way the same family has run the establishment for decades. It's also the name of one of Wisconsin's most beloved cocktails, which the restaurant's bartenders strive to perfect.



    Inside Tips

    • All of Jackson Grill's dinners come with housemade soup. If you get the opportunity, select the crab bisque, which has received praise from both Third Coast Daily and the Milwaukee Journal Sentinel.
    • Arrive hungry. In addition to soup, each dinner also comes with salad, a breadbasket, and a complimentary bowl of olives. The entrees are also so big that you "might have to call in reinforcements for desserts," according to the Milwaukee Journal Sentinel.

      While You're Waiting

      • Check out the collection of framed signatures from local celebrities and venerated Wisconsin athletes in the foyer. A few of these famous folks are regulars, so try not to kiss the autographs in case they see you.
      • Try to spot Chef Jackson. He's been known to make the rounds in the dining room, chatting with guests and asking how their nights are going.

3736 W Mitchell St
Milwaukee,
WI
US

Hard as it is to hold off on the pizzas at Tarantino, it might be worth it if it means a chance to try the appetizers. Diners can begin by splitting orders of mozzarella sticks, buffalo wings, or eggplant strips. Then it's time to dig into one of the specialty pies, such as the Mexican pizza: mozzarella and cheddar cheese topped with ground beef, black olives, and onion. Pastas include lasagna, mostaccioli, and ravioli, the latter of which comes stuffed with meat, spinach, or cheese, and never a note that says, "IOU one ravioli stuffing."

2577 S 68th St
Milwaukee,
WI
US

Brewski's Sports Club can only be described as an adult playground. Giant screens broadcast popular sporting events, including football and baseball games. Black lights dangle over long tables set up for drinking games. A hoops game helps patrons work on their jump shot. On Sundays, bartenders mix up liquid breakfasts, including the Eggs and Bakey, a bloody mary mix paired with house-infused bacon vodka, topped with a hard-boiled egg, and loaded with cheese whips and bacon.

6024 W Bluemound Rd
Milwaukee,
WI
US

5 O'Clock Steakhouse: A User’s Guide

Award-Winning Steak House | Classic Surf 'n' Turf | Live Entertainment | Californian Wines | Supper-Club Decor

Sample Menu

  • Appetizer: shrimp cocktail
  • Entree: bacon-wrapped fillet with blue cheese
  • Drink: Rodney Strong merlot from Sonoma

When to Go: Try to plan your dinner for a Friday night around 8 p.m. That’s when musicians hit the adjoining Alley Cat Lounge stage, playing everything from oldies and jazz to modern rock and R&B.



Inside Tip: Show up hungry. All meals come with a salad, relish tray, and sourdough bread with butter and honey. A side of butter-sauteéd mushrooms also accompanies every steak.



Media Mentions: Over the years, 5 O’Clock has drawn national attention. The Travel Channel featured it on the program Steak Paradise, Saveur magazine named it one of the best steak houses in the country, and Travel + Leisure said it has a "Mad Men vibe."



Behind the Name: According to the restaurant's lore, the steak house got its name from an alarm clock that would ring every day at 5 p.m., alerting customers that it was time for a free drink.



While You’re in the Neighborhood
Before: Tour the Tripoli Shrine Center (3000 W. Wisconsin Avenue), a replica of the Taj Mahal and a member of the National Register of Historic Places.

After: If the entertainment at the Alley Cat Lounge isn't to your taste, head over to The Coffee House (631 N. 19th Street), which offers acoustic music and poetry performances.

2416 W State St
Milwaukee,
WI
US

Mr. WEBO's sets itself apart from run-of-the-mill taquerias with their full service outdoor patio and their colorful, urban murals depicting everything from diamond-studded roses to a skeleton mariachi band. The graffiti-chic decor is counter-balanced by a refined menu of updated Mexican classics made fresh-to-order with many local ingredients. Standard baja fish tacos, for example, are re-imagined with a tangy breading made from yellow and blue cornmeal, then topped with shredded purple cabbage, chipotle aoli, and avocado crema. Meanwhile, chiles rellenos arrive dredged in a corona batter and stuffed with green and red chorizo, and flourless gluten free chocolate cake awaits to provide a sweet ending to spicy meals or post-dinner food fights. One taqueria tradition Mr. WEBO's has loyally adhered to? Margaritas––which are served by the whole- or half-pitcher in a choice of six flavors.

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2301 South Howell Ave.
Milwaukee,
WI
US

Property Location
Located in Milwaukee, DoubleTree by Hilton Hotel Milwaukee Downtown is minutes from Frontier Airlines Center and Milwaukee Public Library. This hotel is within close proximity of Milwaukee Public Museum and U.S. Cellular Arena.

Rooms
Make yourself at home in one of the 243 air-conditioned guestrooms. Complimentary wireless Internet access is available to keep you connected. Bathrooms feature shower/tub combinations, makeup/shaving mirrors, and designer toiletries. Conveniences include safes and complimentary newspapers, and housekeeping is provided daily.

Rec, Spa, Premium Amenities
Take advantage of recreation opportunities such as a 24-hour fitness facility, or other amenities including gift shops/newsstands and shopping on site. Additional amenities include wedding services and a television in the lobby.

Dining
Grab a bite to eat at the hotel's restaurant, which features a bar, or stay in and take advantage of room service (during limited hours). At the end of the day, relax with your favorite drink at a bar/lounge. Hot/cold buffet breakfasts are available daily for a fee.

Business, Other Amenities
Featured amenities include a business center, audiovisual equipment, and express check-in. Event facilities at this hotel consist of conference/meeting rooms, small meeting rooms, and a ballroom. Parking (subject to charges) is available onsite.

611 W Wisconsin Ave
Milwaukee,
WI
US